Concerts Reviews
Conan Gray Turns Bridgeport Into a Wishbone Dreamland
On Friday, September 19, 2025, the Hartford HealthCare Amphitheater in Bridgeport transformed into Conan Gray’s whimsical playground for the only New England stop of his Wishbone Pajama Show tour. The sold-out crowd arrived ready, many dressed in pajamas or sailor suits to match the tour’s theme. Some fans swapped friendship bracelets, while others passed around handwritten notes to be delivered to Gray. The energy was buzzing long before the show began, with the amphitheater erupting into singalongs to pre-show playlist staples like ABBA’s “Dancing Queen” and Olivia Rodrigo’s “Bad Idea Right?”
The evening opened with hemlocke springs, the project of Isimeme Naomi Udu. Her mix of 80s-inspired synths, 2000s pop sparkle, and the occasional emo-rock edge made for a charismatic half-hour. She even teased a few unreleased tracks, which had the audience leaning in.
At 9 p.m., the lights dimmed and the screams reached their peak. Conan Gray appeared riding a red Schwinn bike, pedaling across the stage before hopping off to grab a microphone out of a mailbox marked with “Bridgeport” and the night’s date. Backed by his band in sailor suits, Gray launched into “My World,” the first track of a night carefully structured into four themed acts.
The staging was ambitious for an amphitheater show. Act I, “a wishbone never breaks even,” featured a rustic set complete with a windmill and wheat fields, framing songs like “Never Ending Song” and “Wish You Were Sober” as moments of nostalgia and longing. By Act II, “i got the short end of the stick,” Gray changed into shimmering pajamas while a giant bed and clouds floated across the stage. Songs like “Class Clown” and “The Cut That Always Bleeds” leaned into intimacy, with the crowd often singing louder than the performer.
Though Gray doesn’t rely on heavy banter, he has a knack for making fans feel seen. That connection was clearest during Act III, “i took the long way to realization,” when he pulled out the tour’s signature ritual: breaking a wishbone to determine the surprise song. Former NFL player Carl Nassib joined him on stage to help with the pull. The wishbone split perfectly down the middle, leaving Gray to laugh at the coincidence before choosing to debut “Care” live. That moment, sandwiched between heartfelt renditions of “Romeo” and a haunting extended version of “Heather,” stood out as the night’s highlight.
The final act, “i wished for love, and I found it,” leaned into pure pop. For “Actor” and “Maniac,” Gray and his band stretching the intros and savoring the chaos. “Vodka Cranberry” closed the main set with confetti cannons and a sea of phones lighting up the amphitheater.
Gray returned for a two-song encore, delivering “Memories” and “Caramel” with just enough sweetness to balance the night’s theatrical highs.
Conan Gray has come a long way from his YouTube beginnings. With Wishbone, his fourth album, he’s leaned into big staging and narrative-driven concerts without losing the intimate, confessional spirit that made fans fall for him in the first place.
Upcoming Tour Dates:
September 22 Hollywood, FL Hard Rock Live
September 24 Nashville, TN Ascend Amphitheater
September 26 Charlotte, NC PNC Music Pavilion
September 28 St. Louis, MO Hollywood Casino Amphitheater
September 29 Kansas City, MO Starlight Theatre
October 1 West Valley City, UT Utah First Credit Union Amphitheatre
October 3 Mountain View, CA Shoreline Amphitheatre
October 4 San Diego, CA Viejas Arena
October 6 Morrison, CO Red Rocks Amphitheatre
October 16 Mexico City, MX Palacio de los Deportes
October 17 Guadalajara, MX Auditorio Telmex
October 19 Monterrey, MX Auditorio Banamex
More information here.
Check out our favourite photos of the night below or head to our Facebook page for the full gallery!
CONAN GRAY
All Photo Credit: Sophia Riseman
